Development of dynamic kinetic resolution on large scale for (±)-1-phenylethylamine

Candida antarctica lipase B (CALB) and racemization catalyst 4 were combined in the dynamic kinetic resolution (DKR) of (±)-1-phenylethylamine (1). Several reaction parameters have been investigated to modify the method for application on multigram scale. A comparison of isopropyl acetate and alkyl...

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Bibliographic Details
Published in:Beilstein Journal of Organic Chemistry
Main Authors: Lisa K. Thalén, Jan-E. Bäckvall
Format: Article in Journal/Newspaper
Language:English
Published: Beilstein-Institut 2010
Subjects:
dynamic kinetic resolution
kinetic resolution
racemization
Shvo
Candida antartica lipase B
Science
Q
Organic chemistry
QD241-441
Antarc*
Antarctica
antartic*
Online Access:https://doi.org/10.3762/bjoc.6.97
https://doaj.org/article/3b65cf5ea3e1476bb9ced3c1d9fb9651
Description
Summary:Candida antarctica lipase B (CALB) and racemization catalyst 4 were combined in the dynamic kinetic resolution (DKR) of (±)-1-phenylethylamine (1). Several reaction parameters have been investigated to modify the method for application on multigram scale. A comparison of isopropyl acetate and alkyl methoxyacetates as acyl donors was carried out. It was found that lower catalyst loadings could be used to obtain (R)-2-methoxy-N-(1-phenylethyl)acetamide (3) in good yield and high ee when alkyl methoxyacetates were used as acyl donors compared to when isopropyl acetate was used as the acyl donor. The catalyst loading could be decreased to 1.25 mol % Ru-catalyst 4 and 10 mg CALB per mmol 1 when alkyl methoxyacetates were used as the acyl donor.

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